Scheme 2.

Development of the C₂, C₃, C₁₀ Stereotriad of 16.a

^aReagents and Conditions: a) DIBAL, CH₂Cl₂, −78 °C, 98%; b) PMBCl, NaH, DMF, 0 °C to rt, 97%; c) 1M HCl, MeOH, 100%; d) TBSCl, imidazole, CH₂Cl₂, 92%; e) 14, EDCI, DMAP, CH₂Cl₂, 97%; f ) TMSCl, Et₃N, −78 °C, then LDA, −78 °C then reflux, 85%, dr = 94:6; g) DDQ, CH₂Cl₂, H₂O, 0 °C; f) EDCI, DMAP, CH₂Cl₂